Renin inhibitors
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preparation 1
Weinreb Amide
(R)-tert-butyl 3-(N-methoxy-N-methylcarbamoyl)piperidine-1-carboxylate
[0200]
[0201](R)-1-(tert-butoxy carbonyl)piperidine-3-carboxylic acid (25 g, 0.11 mol, 1.0 equiv), N,O-dimethylhydroxylamine hydrochloride, (10.5 g, 0.14 mol, 1.25 equiv), EDC.HCl (26.3 g, 0.14 mol, 1.25 equiv) and DIEA (48 mL, 0.28 mol, 2.5 equiv) were dissolved in CH2Cl2 (400 mL) and stirred overnight at rt. The reaction mixture was diluted with EtOAc, washed with 5% aq HCl (2×150 mL), satd aq NaHCO3 (150 mL), brine (100 mL), and dried over Na2SO4. Concentration afforded (R)-tert-butyl 3-(N-methoxy-N-methylcarbamoyl)-piperidine-1-carboxylate (24.42 g, 82%) as a clear oil.
preparation 2
Halodiphenyl Ethers from Halophenols and Benzeneboronic Acids
1-(3-Fluorophenoxy)-2-bromobenzene
[0202]
[0203]To a stirring solution of 3-fluorophenylboronic acid (2.10 g, 15 mmol), 2-bromophenol (1.77 g, 10 mmol) and Cu(OAc)2 (0.93 g, 5 mmol) in anhydrous CH2Cl2 (25 mL) is added activated 4 Å molecular sieves (˜0.1 g), followed by anhydrous Et3N (3.5 mL, 25 mmol). The resulting dark green solution is stirred at rt for 48 h. The mixture is evaporated under reduced pressure and the residue washed several times with Et2O (˜150 mL). The Et2O solution is washed with satd aq NH4Cl and 1 N aq HCl. The organic layer is evaporated and the crude product is purified by flash column chromatography to give 1-(3-fluorophenoxy)-2-bromobenzene (1.28 g, 48%) as clear oil.
[0204]The following halodiphenyl ethers were prepared following the procedure described above.
Halodiphenyl etherPhenolBoronic Acid1-bromo-3-chloro-2-[(2-2-bromo-6-chlorophenol2-methylphenylboronic acidmethylphenyl)oxy]benzene1-bromo-3...
preparation 3
Halodiphenyl Ethers from Phenoxyanilines
1-(O-tolyloxy)-2-iodobenzene
[0205]
[0206]To a solution of 2-(o-tolyloxy)aniline (40 g, 0.2 mol) in 1N aq HCl (400 mL, 0.4 mol, 2 equiv) cooled to 0° C. was added dropwise a solution of NaNO2 (18 g, 0.26 mol, 1.3 equiv) in water (520 ml). The mixture was stirred for 1 h at 0° C. and a solution of KI (83 g, 0.5 mol, 2.5 equiv) in water (500 mL) was added dropwise with vigorous stirring. After 0.5 h the mixture was warmed to 90-100° C. for 1 h, cooled to rt and washed with satd NaHSO3 until the aqueous layer became clear. The mixture was extracted with EtOAc (3×200 mL) and the combined organic layers were washed with aq Na2S2O4 and dried over Na2SO4. After evaporation of the solvent, the solution was passed through a short silica gel column to afford 1-(o-tolyloxy)-2-iodobenzene (40.0 g, 65%).
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